Pity Sex
by WizMonCruWil
Summary: This is a quick little thing I wrote. Neville is a virgin. When he feels more impotent than his more sexually experienced friends, he will turn to a beautiful, intelligent witch for help. Will Hermione give him the help he seeks? Read to find out. Enjoy!
1. Chapter 1: Measuring Contest

**Chapter 1: Measuring Contest**

It was a late night in the Gryffindor Common Room. The sixth year boys were all staying up, talking about the most popular topic with men their age: girls.

"Who here has gotten shagged in the sack?" Seamus Finnegan called out.

Harry Potter, Ron Weasley and Dean Thomas all raised their hands. However, Neville Longbottom's hand remained noticeably, embarrassingly, by his side. The Herbology protege blushed when Seamus made a point of calling him on it.

"Never been shagged, have you, Longbottom?"

Neville flushed and shook his head.

"Ever been given head?"

Another denial.

"A wank?"

"With what, mate? His own lilly-white hands?" Dean cackled. Harry punched him on the arm, indicating the teasing was getting a little out of line. For his part, Neville remained silent in affirming his inexperience with all of these. He was a virgin in the purest sense... and had no idea if that streak would ever be broken.

That didn't mean he didn't dream, fantasize about girls. There were several good candidates that he fancied, and one strikingly beautiful witch in particular.

All alone in his four-poster bed that night with the curtains drawn, Neville humped his pillows as he thought of her bushy brown hair framing around her round, pretty face like a halo. He thought of her beaming smile, the way she bit her lip whenever she answered a question in class. The confident air in her svelte body as she cast a spell. Her nice, surely soft skin. Her cute arse swiveling in those tight jeans as she walked. Hermione Granger's piercing brown eyes... those full lips...

Neville's entire body seized as he thrust a little too hard and too long. He felt the muscles in his organ pulse, and a sticky substance coat his legs. He had jizzed all over himself. Slipping into the bathroom, he cleaned himself before returning to bed without waking the other boys. Placing the rumpled pillow back under his head and rolling over, he went back to sleep.


	2. Chapter 2: Will You Sleep With Me?

**Chapter 2: Will You Sleep With Me?**

Over the last several weeks, Hermione had noticed Neville showering her with more and more attention.

When he complimented her outfit one morning at breakfast, she had been startled, but nevertheless appreciated the gesture. But when Neville also made a point of admiring her earrings a few days later, that is when she began to detect a pattern.

Now, this morning while reading by the Black Lake, she spotted Neville approaching her with a shy countenance about him. She smiled brightly. Before she could ask why he was there, he held out a small box.

"Here, I-I thought this would look good with that purple jumper you got last year." He stuttered and his face flushed.

Eyeing him, she accepted the box and pulled it open. Inside was a beautiful gold chain holding a charm. Hermione held it up and studied the pendant. It was a delicately made relief of a wand, a spell bursting from its tip like a sun. In the center of the burst sat a chip of purple gemstone. She stared at it until Neville fidgeted and she looked back at him.

"It's lovely Neville." She smiled for a heartbeat and then narrowed her eyes at the blushing man. "Now, what's going on?"

"No-nothing." He stuttered, blushing again.

"Yes there is. You complimented me twice and just gave me a necklace, now out with it." She gave him her best teacher look. It must have worked because he spoke.

"I wanted to ask a favor of you." She arched an eyebrow until he continued.

"Willyousleepwithme?" He said it all in one go, face going as red as a Weasley's hair.

"Excuse me?" Hermione was fairly certain she had understood him the first time, but it was entirely out of character for the shy and bumbling student.

Neville launched into a nervous rambling explanation. "I'm a virgin and you're one of the few nice girls - women I know. And-"

Hermione cut him off. "Neville, I get the idea." She didn't know if she should laugh or be offended. "Yes, all right, then. I'll do it." She was surprised to hear the words escape her lips without her permission.

Neville looked up in shock. "Really?" The red was slowly dissipating from his face to be replaced with a nervous green tinge.

"Yes. Let's go now."

Neville grabbed her hand and pulled the brunette to her feet. His skin was clammy against hers as he led her back into the castle and up the stairs to the boys dormitory in the Gryffindor Common Room. Despite it being the middle of the day, the room felt cold somehow. A shiver slid down Hermione's spine and she quickly wiped her hand on her dress.

Once the door was closed and locked, Neville seemed to have lost steam and just stared blankly at the shorter woman. Hermione desperately wanted to flee back out the door but she had agreed and wasn't about to back down. She didn't bother to speak as she approached Neville's four-poster bed and drew her wand. She scourgified the bedding, tapped her stomach with her wand, then banished her clothes to a neat pile on the floor and quickly slipped between the sheets.

She could feel the butterflies in her stomach but Neville looked like he had something more substantial trampling around his insides. The beautiful witch didn't have time to encourage her classmate as he seemed to discover the bit that made him a Gryffindor as he went around the other side of the bed, charmed the limp curtains closed and his clothes to the floor. He jumped into the bed just as quickly as Hermione had.

They lay there silently for a moment, fidgeting slightly. Hermione accidentally brushed her hand against her classmate's hip and they both jumped. Neville suddenly cleared his throat with a slight squeak. Hesitantly, Hermione rolled over him so that she was straddling his waist. She had never been with a man, but she had read many medical books and some fiction and thought she knew what to expect. Regardless, the warm feeling of his member against the inside of her thigh made her gasp in surprise.

Trying to keep her eyes tender and kind, Hermione gently kissed Neville on the mouth. He chastely kissed her back, and did not try anything untoward and she was glad, but he was breathing heavily in her ear. Carefully she shifted her hips to align better with his and she felt something cold and sticky touch her skin. Hermione had to squeeze her eyes shut to keep the whine of revulsion from passing her lips. And then Neville was flipping them both over so that she lay beneath him, nudging her legs wider, slipping inside her. The pain of her womanhood being stretched came, making Hermione gasp in pain, but it wasn't as sharp as she had expected. She didn't yelp or cry out, as she might have imagined when she was first defiled. Slowly, Neville began to rock his hips into Hermione, working up a thrust. But the rhythm was desperate, inconsistent, clumsy. Drawing Neville closer, Hermione shut her eyes and kissed him deeply, hoping that such intimate affection would help them through the awkwardness.

Hermione didn't know if he had a girlfriend. She hadn't thought to inquire. Surely not, otherwise he wouldn't have asked to sleep with her! She wondered what had possessed Neville to seek out this fulfillment. Maybe from his roommates, but did they talk about their conquests? Harry was above that, and though he could be a bit of a tosser, Ron would never be that crass, either. All she knew was that Neville wasn't entirely here, with her. Not as his knees brushed up against the mattress, occasionally knocking against hers. Not as her hair caught in his fist when he bunched the bedclothes up. Not feeling her lips brush his lips, his chin, his collarbone as he bore down. He couldn't hear her increasingly pathetic moans - some dragged into being out of pleasure, but more out of discomfort. Hermione focused on her breathing, which was becoming increasingly shallow. Neville's grunts and the sound of their naked, sweaty skin slapping and colliding. Hermione concentrated on the feeling of the hot flesh in the small of his back and along his ribs where her legs gripped him. It was not a very long time before Neville stiffened, his form quivering as he let out a sound like none she had ever heard before flopping bonelessly on top of her, his head lolling forward in between the valley of her breasts.

"Was it in?" Hermione asked, confused. Though she knew from the sharp, stabbing ache now gathering between her legs that he had indeed penetrated. None of it had felt like she had read about.

He nodded and sighed contentedly. "That was amazing. Thanks, Hermione."

He rolled off of her, and lay still and quiet. Hermione felt disgusted with herself - not Neville, necessarily, just herself - and threw the covers back, launching towards the bathroom. The beautiful witch jumped into the shower, thanking her lucky stars that the boys' dormitory actually had hot water. She scrubbed her skin red and raw, using all of the bar of soap she had conjured. By the time she was done, the water had cooled and her fingers were wrinkled. Holding the towel around herself tightly, Hermione peeked around the bathroom door towards the bed. Neville was sprawled across the mattress, fast asleep on his back with the sheets kicked down past his knees.

Having left her wand on her pile of clothes, Hermione silently approached the bed and began dressing, trying to keep her eyes away from her impromptu bed partner but she couldn't help sneaking a peek at her friend.

Hermione had seen illustrations of naked men, and had caught various glimpses of Ron and Harry when they went swimming or forgot to close the bathroom door completely. But Neville didn't look quite like what she had seen. In all honesty, he was tiny.

Well, overall he was taller than her, but below the belt, his willy was barely visible through his black pubes. Knowing men were usually very self conscious about their size, Hermione stifled a giggle and quickly finished getting dressed before apparating back to the grounds. Finding her favorite reading tree, she curled up in the spot, wincing at the stab of pain between her legs as she sat back in the grass. Opening back to her page, she resumed reading, even as her mind wandered back over her first time. Whether she liked it or resented it. A part of her regretted it, but the one silver lining had been that it had been with Neville. A kind boy who would never dream of hurting her.

She supposed that's where the pity in "pity sex" came from.


End file.
